Hydrochloric Acid → Ethyl N-methyl-N-(4-nitrosophenyl)glycinate

HRID 381207

反応式

HRID 381207 の反応式
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[N:16]([O-])=[O:17].[Na+].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][N:2]([C:9]1[CH:10]=[CH:11][C:12]([N:16]=[O:17])=[CH:13][CH:14]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 265936(Methyl-phenyl-amino)-acetic acid ethyl esterHCID 23668193Sodium Nitrite

生成物 1

HCID 12038854Ethyl N-methyl-N-(4-nitrosophenyl)glycinate

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A solution of 15.5 g (80 mmol) of ethyl N-methyl-N-phenylglycinate in 80 g of ice and 40 mL of conc.HCl was stirred at 0-5° while a solution of 6 g (87 mmol) of NaNO2 in 40 mL of water was added dropwise over 30 min. After stirring at this temp. for 1 hr, a solution of 27 g (250 mmol) of Na2CO3 in 150 mL of water was added dropwise with cooling. The green solid was collected, washed with cold water, extracted into CH2Cl2, passed thorugh silica with CH2Cl2 to remove an impurity, and the product eluded with 10% ethyl acetate/CH2Cl2 to give 14.7 g (66 mmol, 83%) mp 55-56° after washing with 10% ethyl acetate/hexane. Anal. C11H14N2O3 (222): Calcd.: C,59.45; H,6,35; N,12.60. Found: C,59.46; H,6.14; N,12.49. MS(FD) m/z 222. 1H NMR(CDCl3)δ: 7.8,broad s,2H,ArH; 6.69,d,2H,ArH; 4.22,q,2H,CH2—O; 4.20,s,2H,CH2—N; 3.23,s,3H,CH3—N; 1.27,t,3H,CH3—C.

後処理

  1. additionwas added dropwise over 30 min
  2. temperaturewith cooling
  3. customThe green solid was collected
  4. washwashed with cold water
  5. extractionextracted into CH2Cl2
  6. customto remove an impurity
  7. customto give 14.7 g (66 mmol, 83%) mp 55-56°
  8. washafter washing with 10% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-a27d2fba9a484020bd8e16469f247277
出典データセット
uspto-grants-2001_10
特許番号
US06306570B1

関連ノート

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